Readers often email us asking us for advice about new businesses they are thinking about starting and we often find that many of them don’t have a framework for thinking about a more fundamental question: why should or shouldn’t you start a business?

Below, you’ll find how successful entrepreneurs from across the city thought about this very question when they were considering whether to start their businesses.

Monique Whitley Phillip | Mental Health Counselor & Practice Owner

The thought process in creating Jars of Clay, A Sanctuary has been to create a place where women would feel safe enough to receive comfort and reassurance, while building or re-building a life structure for themselves that would sustain them. Because of my clinical background in mental health, the most natural way for me to do that was to create a private practice solely focusing on women’s issues, with the mission of helping them uncover the things about them that make them valuable. Read more>>

Leslie Tankersley Arboleda | The Kizen Koach – executive and relationship life coaching

This current iteration of my business, Kizen Living, is much like me, personally – it is the result of many revisions and it has been recreated many times to truly reflect my passion, purpose, and power. Read more>>

Sierra Cooley | Social Media Manager & Content Creator

When I started my Social Media Management and Content Creation business *officially* in February of 2023, I gave myself no other option than to succeed. I have always struggled with extreme anxiety, so leaving a stable corporate position in order to pursue my passion full-time… was terrifying, to say the least. Read more>>

Karina Myers | Maker & Artist

I’d always dreamed of being able to create art for a living. I grew up selling small handmade items at homeschool craft fairs, garage sales, and fundraisers, and I loved it! I think it was a natural progression for that love or creating and selling art and handmade items to develop into a business as an adult. Creating something beautiful and meaningful is incredibly fulfilling for me, and I love seeing how my passion touches the lives of others and brings them joy. I’m also both a homebody and a pretty spontaneous, go with the flow personality, so the idea of a career that allows me to have time and location freedom while getting paid to do what I love is incredibly exciting, and a huge motivation for me to run my own business! Read more>>

Lee Calisti | Architect

It was the collision of a series of life events – simple and complex. However, to put it simply, my son was born in 2002 while I worked in Pittsburgh, with over an hour’s commute each way. Once I saw him, I fell in love and wanted to be with him all the time. In early 2003, I was on my own, starting a business. Read more>>

Kris ‘KBOT’ Webster | Chief Metaverse Officer Of The Avatar Convention Center & Robot Puppet Show

For much of my life I did things to please others 1st. What I found out is that can be foolish because as soon as you achieve what others expect of you, they move the goalpost to something else. This can also happen in the workplace. And so, after being laid off during the housing bubble from my corporate office job, I decided to become an entrpreneur and figure out ways to make multiple sources of income. Read more>>

Jackie Wachter | Cofounder and Creative Director of FOUNT Leather

My husband and I started FOUNT nearly ten years ago when I grew tired of the straps breaking off my bags. Anytime I would go to the shoe cobbler, there would be a plethora of bags, many of them being high-end designers, waiting to be repaired. I couldn’t believe that these notable brands did not have a guarantee on their product and that for the price women were paying – these bags were not holding up. Read more>>

Lexi Matthews | Owner / Operator

We both lost our jobs at the beginning of COVID in the music industry (Lexi) and as a chef (Rex) in Chicago. We were sitting around twiddling our thumbs in our tiny apartment and decided to move back to my (Lexi) hometown of Marion, IA. My parents own the building our coffee shop is in and the previous tenant has just backed out of their lease. When I first started my job at a music agency I told the interviewer, if I don’t work in music, I want to be an entrepreneur. It felt like right time, right place, and with a bit of safety net even though it was probably the worst time to open a business. Read more>>

Nancy Hayes | Owner & Intuitive Practitioner

I wanted to be able to provide this work for people that wanted help in these areas but perhaps had not really seen themselves in this work. As a first-generation Mexican American woman, I know there is a lot of stigma in our culture for those who don’t follow the religious path. I also recognize that what I do is nothing new, and it is in a lot of ways a circling back to our ancestral roots, but it can feel very challenging to break away from the current cultural expectations. Read more>>

Megan Bello | Managing Broker Owner

When I choose to go into Real Estate, I wanted to create a career that would allow me to raise my children when I had them while also being able to be involved in the industry. I choose Real Estate because it was a few weeks of classes with a sales license that had no cap on earnings. I had spent the last few years in outside sales and was able to see the direct correlation for what I was doing for their business that helped them grow and make more money, so I wanted to set out and create my own money for my own brand and business. Read more>>

Agostina Zampieri | Artist

I started traveling the world early on in college, funding my trips with side gigs. I tried a “real job” two years after I graduated as an architect, that lasted me about a month. I consider myself a free soul and being told what to do, or having to request off to go on a trip made me feel like a bird inside a cage. Creating my own business was not something that I thought of, it was just a destination in my pursuit of freedom. Read more>>

Leticia Raymond Darius Reed | Owners and Operators

I understood that starting my own business was going to be a challenge, I knew that taking on a second business would be even bigger. I started The Carefree Pup in 2016 and worked hard to build that business into a flourishing entity, I knew Darius and I could do the same by taking on Crown Boulder. We both knew we wanted to take on an exisiting business and giving it our own touch, we also knew that it would take time, commitment, and effort, even some tears, to earn the trust of exisiting clients and develop relationships with new connections as well! We wanted to be in an industry and fed both our souls and kept us connected to the communities we’ve been a part of for years. Read more>>

Melissa O’Malley | The Self Care Witch

After earning a masters degree in clinical counseling in my early 20’s, I started my career working for my town’s great big counseling agency. I made a nice salary, trainings and supervision were free to me, and in many ways, it was exactly what I always dreamed of. I had a big office, a caseload of clients who loved me, and my coworkers were pretty great too. I had always been a casual student of astrology and witchy things, but it was a quiet part of my life, and totally separate from my work as a counselor. Then, on one ordinary and magical Tuesday, a witch gifted me my very first Tarot deck, and the entire trajectory of my life changed. Learning the Tarot provided a pathway to healing my own anxiety and trauma that I never could have imagined possible. As I grew into my own intuitive knowing, I witnessed firsthand the healing that comes from connecting to your power while simultaneously surrendering to your human-ness. The Tarot provided me insight into how I was interpreting and operating in my world, and gave me clear anchors and guideposts to help me decide how to show up in my power. Read more>>

Brandon Couden | Gym Owner/Coach

Starting the business actually wasn’t a long-term plan; it was more of a pipe dream for me while working at an athletic/group training facility as a trainer and occasionally substituting as a teacher. I was broke, living paycheck to paycheck, so gathering funds to start a gym wasn’t at the forefront of my mind. However, everything changed when another trainer and I were purchasing equipment from what was then a Gym/Equipment company known as Rogue Fitness. Read more>>

Quinzel Harding | Upholstery Service

My thought process starting the business was always about ownership for the hard work that would eventually build a brand to feed my family and other families. I started off working at a local trim shop here in the Colorado Springs seeing myself working hard for the company, and how much money I had earned them it was time for me to give it a shot. Out of my 1 bedroom apartment is where the thought process of becoming a business owner became real. I knew for my family to achieve real wealth is through building a reputable brand, while also loving what I did always made the business idea. I truly enjoying sewing so it never feels like work. I knew I had to make a reality to live my doing what I love. Read more>>

Jason & Victoria Birdsong | Artists & Owners

Jason: As far as ‘Art’ goes, I began drawing when I was really young, I had a rough childhood but was adopted into an amazing family when I was 8, and I have enjoyed art; it acted as a good outlet for my young self and became something I really enjoyed. I have been in galleries in several cities across the South; which is where I’m from, Louisiana, but when I moved here 2 and half years ago, I struggled to find one in the Denver area that would really give me a chance or even the time of day. Read more>>

Nicolas Dromard | Singer, Dancer, Actor, Entertainer

After performing on Broadway for over 15 years, we decided to create our two person show, our own brand/business to do what we love and create our own work. Read more>>

Matt Croghan | Owner

My wife and I moved to Salida, CO, from Denver with our two month old daughter. I was a stay at home dad and looking to start a side business to keep myself busy outside of family duties. We started growing microgreens when I was diagnosed with Celiac Disease shortly after moving to salida in order to boost our diets nutritional content. We found them so helpful that we started Poncha Creek Gardens to share microgreens with our community and beyond. Read more>>

Rick & Stephanie Osborne | Wedding Photographers

My husband Rick and I both come from entrepreneurial families. Working hard and taking risks to own and operate your own business were both modeled to us from an early age. I had been freelancing for newspapers throughout Southern Colorado. I started photographing families and weddings on the side while also keeping a full time job where I met Rick. Rick is such a driven and hard working person who also happened to be an amazing artist. He was super creative, learning how to use a camera gave him an outlet to use his artistry in a way that was lasting and made a big impact on the world. Photography is personal, artistic and makes a real impact on the lives of people. We officially decided to take the leap and quit our day jobs 15+ years ago! While there have been busier years and some that were slower, it has been such an amazing blessing that God has allowed us to make a living doing something we love! Read more>>

Jill Van Slyke | Business Owner | Skier

A few years back, I was looking for a change with a better work/life balance and had started thinking of transitioning out of a more corporate environment. My family happened to come across this really awesome company, Purl, that had been around since 1999. The opportunity to acquire it kind of fell into our lap at a good time… and I just took a leap of faith in doing something new! It fit in with a lot of areas that I’m passionate about: outdoors, snow sports, wanting to run my own company while having a more flexible schedule to spend more time on the mountains and with my family. Read more>>

Air Gustafson | Corporate Hamster turned first time Petpretnuer

I created Morty’s Bark & Brew as a platform where dogs take center stage, where they aren’t just an afterthought but the heart and soul of our community. At Morty’s, our mission is crystal clear; to carve out a space where dogs aren’t just existing, but truly thriving in a world largely designed for humans. We are here to flip the script, ensuring our furry friends aren’t relegated to the sidelines but are celebrated as the main event. It’s all about unleashing the boundless joy, energy, and companionship that dogs bring to our lives. Let’s give back to our pups in the same generous and genuine way they give to us every day! Read more>>